Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me at dating.itscomplicated[at]!


Recently I was watching the opening ceremony for the Olympics with my girlfriend and her mom. Seeing as how we are in high school we find it hard to keep our hands off of each other. During the commercials her mom leaves the room to go make popcorn and my girlfriend instantly jumps on my face. After making out for a few seconds she pulls away in disgust. Both of our faces are covered in blood. As soon as we discover which one of us is bleeding profusely out of their nose (of course its me) her mom comes back into the room and is welcomed by the sight of her daughter's face smeared with blood. We both ran to the bathroom and cleaned ourselves up and then explained the situation. I would love to know what went through her mom's head during that first second when she saw us…



I broke up with my girlfriend because I was not ready for a child and she was demanding one.  I then knocked-up a girl I had a one night stand with three weeks later.


Let me begin by saying I’m 6’1”, 180lbs, and for no apparent reason, my ex-girlfriend that I dated for over 2 years was convinced that I was going to become fat.  Last year towards the end of second semester, my roommates and I were having a bonfire with some casual beers, hot dogs and s’mores.  My then girlfriend decided that she was invited and showed up.  I ate a hot dog, drank a beer, and began preparing another hot dog, when she looked me dead in the eye and asked in all honesty, “Really?..….another hot dog?”  We broke up the next day.  What a great 2 years of my life.


When I broke up with my last girlfriend, she told me that I played too much World of Warcraft, and would never do anything worthwhile with my life. I just found out that she's dating my guild leader from when I played World of Warcraft, who dropped out of college to have more time playing WoW, and who's current job is working security at Eagles games when he's not too hungover to get there… I stopped playing WoW and am going to law school next year.



A couple years back living in my parents basement, I hooked up with my ex-girlfriend on a booze filled night… things went from hot to steamy and before you know it I had her clothes off and tossed into the dark… little did we both know that the basement wall was leaking water and there was a stream forming under my bed… it wasn’t until I went searching for her clothes did I find her sopping wet jeans and panties swimming upstream.  I had to send her home wearing a pair of my pants…too bad I’m a big 6'2" and she's a petite 5'3" and that her mom answered the door when I dropped her off…

My dumbass ex just sent me an email about how upset he is that we broke up and how I broke his heart, how he had never been alone on valentines. He ended it by saying happy valentine’s day bitch. I emailed him back that valentine’s day was the 14th, he wrote back, "Since when?”

I'm a recent college grad trying to find a job in this craptastic economy.  As such, I'm still living in my parents’ house, and spend most of my time in my basement to generate some space between me and my parents, especially when my girlfriend is around.  One night we were watching tv, and my girlfriend was getting a little frisky.  Thinking both my parents were upstairs and we'd have plenty of warning if either started coming down, she proceeded to undo my pants and go to town.  I did my best to be quiet and we finished up quickly; not thirty seconds later, my Dad, who was quietly working on our computer in the other room, goes running by and up the stairs, closing the door behind him.  My girlfriend and I were mortified… I agreed to go upstairs and apologize.  Instead, I tested the waters; I apologized, and when he said he didn't understand I said "for making out, I though it might have wierded you out."  He said he didn't care and didn't even hear anything… so he says…
-Mike, PA


My girlfriend and I were driving to dinner on our 2nd date. We were having a good time talking while the radio was on in the background. Out of nowhere, and in mid-sentence she suddenly starts laughing. Upon asking her what was so funny, she pointed to the stereo and said, "Oh it's just this song." The song that was playing was Candy Shop by 50 Cent. I asked her why she thought it was so funny and she replied, "A couple months ago, the radio was on while I was having sex. The guy I was with started doing me to the beat of this song and now it just cracks me up." That was in 2004. We're now married.



My parents were out of town and I was watching my little brother. I got him to go to a friend’s house for a sleepover, and I invited my girlfriend over as I would have the house to myself all night.  So we raid my parents’ liquor cabinet, “sample” a bunch of different bottles, strip each other down right there in the living room before taking it upstairs.   So my little brother, across town at his friends house, ate too much pizza and puked so the mom brought him home. They come into the house to find liquor bottles and clothes everywhere.   My awesome little bro thinks quick and says, “Oh, my mom’s home I’m sure. She just likes to drink a lot when she does laundry.” The other mom never said anything.




This week’s “Fight fire with fire…WAIT!  Disregard that statement!  Definitely do not use fire!!!” Award goes to:

My girlfriend is comfortable farting around me… wtf do I do now?

-Anonymous, UWO